CN113122172B - Underfill adhesive suitable for packaging 5G equipment chip and preparation method thereof - Google Patents
Underfill adhesive suitable for packaging 5G equipment chip and preparation method thereof Download PDFInfo
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- CN113122172B CN113122172B CN202011569879.3A CN202011569879A CN113122172B CN 113122172 B CN113122172 B CN 113122172B CN 202011569879 A CN202011569879 A CN 202011569879A CN 113122172 B CN113122172 B CN 113122172B
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/223—Di-epoxy compounds together with monoepoxy compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/24—Di-epoxy compounds carbocyclic
- C08G59/245—Di-epoxy compounds carbocyclic aromatic
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
- C08G59/5026—Amines cycloaliphatic
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
- C08G59/5046—Amines heterocyclic
- C08G59/5053—Amines heterocyclic containing only nitrogen as a heteroatom
- C08G59/508—Amines heterocyclic containing only nitrogen as a heteroatom having three nitrogen atoms in the ring
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/04—Non-macromolecular additives inorganic
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
- H01L23/293—Organic, e.g. plastic
- H01L23/295—Organic, e.g. plastic containing a filler
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/34—Arrangements for cooling, heating, ventilating or temperature compensation ; Temperature sensing arrangements
- H01L23/36—Selection of materials, or shaping, to facilitate cooling or heating, e.g. heatsinks
- H01L23/373—Cooling facilitated by selection of materials for the device or materials for thermal expansion adaptation, e.g. carbon
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2203/00—Applications
- C08L2203/20—Applications use in electrical or conductive gadgets
- C08L2203/206—Applications use in electrical or conductive gadgets use in coating or encapsulating of electronic parts
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Power Engineering (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- General Physics & Mathematics (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Computer Hardware Design (AREA)
- Physics & Mathematics (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Epoxy Resins (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
Abstract
The invention discloses a low-dielectric and high-thermal conductivity underfill suitable for packaging 5G equipment chips and a preparation method thereof. The naphthyl group introduced into the blending modified epoxy resin and the phenyl group introduced into the curing agent have higher molar volume V value, and the cyclohexyl group in the curing agent also has lower molar polarizability P value, so that the dielectric constant of the filling adhesive can be obviously reduced. The mixed heat-conducting filler adopting the spherical graphite and the hollow glass beads can greatly improve the heat-conducting property of the filling adhesive. The method can well meet the severe requirements of the prior high-power and high-frequency 5G communication on equipment packaging materials.
Description
Technical Field
The invention relates to an underfill adhesive for chip packaging, which is particularly suitable for the underfill adhesive for chip packaging of 5G equipment.
Background
The 5G communication technology is a key field of national strategy in China, and the 5G communication adopts millimeter wave band transmission and has the characteristics of rich frequency spectrum resources, high transmission speed, higher data rate, lower time delay, good directivity and the like. These new features place higher demands on the overall performance of the materials used in existing 5G devices. Because the penetration force of millimeter waves is poor and the attenuation is large in the transmission process, if the base material of the 5G equipment is not properly selected, the millimeter waves are in the equipment, so that the delay and the loss caused by the transmission of 5G high-frequency band information, and the transmission energy is also stored in the base material. Based on this, 5G communication requires that the dielectric constant and dielectric loss of the dielectric material used in the device are small, and that the material performance is stable in a wide frequency range. Generally, for 5G devices, the dielectric constant requirement of the materials used is between 2.8 and 3.2, which is much lower than the dielectric constant 3.4 to 3.7 required for 4G devices.
For the chip package of 5G equipment, the underfill used by the equipment is also required to be used as much as possibleThe epoxy resin type filling adhesive which is generally adopted at present for the high polymer material with low dielectric constant can not meet the requirement of 5G high-frequency band transmission. According to the dielectric constant (D) of the polymer material k ) Clausius-Mossotti equation of (D) k ) Proportional to the ratio (P/V) of the molar polarization concentration (P) of the macromolecular functional groups to the molar volume (V) of the macromolecular functional groups. I.e. to lower the dielectric constant (D) k ) That is, the (P/V) ratio is lowered even if the molar polarization degree P is small or the molar volume V is large. In view of the research data and published patents at home and abroad, the current research mainly focuses on the modification of epoxy resin matrix and the composite modification by adding low dielectric constant materials such as microporous aerogel, for example, fluorine-containing, methylene and alicyclic groups are introduced or functional groups with high V values such as phenyl, naphthyl and fluorenyl are introduced to effectively reduce the dielectric constant of high polymer materials. The invention patent with publication number CN111440575A discloses a special low-dielectric high-thermal-conductivity underfill for chip packaging, which adopts epoxy resin with a low molecular weight fluorine-containing polyphenol structure and adds one or more of spherical silicon nitride, aluminum oxide or silicon dioxide and boron nitride to improve the thermal conductivity of the underfill. The invention patent with the publication number of CN111471144A discloses a low-dielectric mixed glue adopting low-molecular-weight acrylic acid modified fluorine-containing polyphenyl ether, and a 5G copper-clad plate prepared by adopting the mixed glue is beneficial to high-frequency and high-speed 5G signal transmission and can be used in the field of next-generation high-frequency and high-speed plates. The invention patent with publication number CN107828358A provides an environment-friendly underfill with low dielectric constant and a preparation method thereof, wherein the epoxy resin is one or any two of hydrogenated bisphenol A type, polycyclic aromatic type and biphenyl type epoxy resin with low halogen content, and hollow glass beads and spherical silicon micropowder are added to greatly reduce the dielectric constant and increase the fluidity.
The invention aims to provide a modified epoxy resin material with a low dielectric constant, which mainly aims at the problems of delay and loss caused by 5G high-frequency band signal transmission by underfill, and simultaneously, spherical graphite is added to improve the heat dissipation performance of the underfill. On the basis of ensuring the heat-resistant performance of high-power transmission, the delay and loss of the 5G signal in the equipment are reduced.
Disclosure of Invention
The invention aims to provide the underfill which is suitable for packaging 5G equipment chips, has a low dielectric constant and is remarkably lower than that of the traditional epoxy resin type underfill, and simultaneously, the added spherical graphite can reduce the dielectric constant and has a good heat conduction effect. The problems of delay, loss, capacity storage and the like caused by high-frequency signal transmission when the traditional filling adhesive is used for packaging a 5G device chip at present can be well solved.
The purpose of the invention is realized by the following scheme:
an underfill adhesive suitable for packaging a 5G device chip and a preparation method thereof are disclosed, the preparation steps are as follows:
step 1: weighing naphthol, benzyltriethylammonium chloride and epoxy chloropropane in a volume ratio of 30:3:67, placing in a reaction kettle, installing a condensing tube, magnetically stirring, reacting at 50 ℃ for 2-4h, and cooling to room temperature; through the form of constant pressure dropping funnel, the control dropping speed is 1d/s, dropwise add and reaction liquid 1: adding a sodium hydroxide solution (C: 7.5mol/L) at a volume ratio of 20-25; reacting at 50 ℃ for 2-4h at constant temperature, cooling to room temperature, washing to be neutral by using deionized water, separating out an organic phase, and carrying out reduced pressure rotary evaporation on the hydrated epichlorohydrin in the organic phase to obtain the phenolic hydroxyl modified epoxy resin.
The reaction formula is as follows:
step 2:
and (2) blending and modifying 10 parts of the low molecular weight naphthol modified epoxy resin prepared in the step (1) and 90 parts of epoxy resin, and sequentially adding 5-10 parts of a curing agent, 10-20 parts of a heat-conducting filler, 1-5 parts of a toughening agent and 0.1-0.3 part of a silane coupling agent according to the proportion of 70-83.9 parts of the blending and modifying epoxy resin. And (3) fully and uniformly mixing in a container, and performing vacuum defoaming treatment to obtain the underfill.
The epoxy resin is one or the mixture of bisphenol A type epoxy resin, bisphenol F type epoxy resin and biphenyl type epoxy resin.
The curing agent is one or the mixture of cyclohexylamine and benzotriazole.
The heat conducting filler is a mixture of spherical graphite with the average particle size range of 1-2 mu m and hollow glass beads with the average particle size range of 3-5 mu m. The mass ratio of the mixture is 1: 1.
The toughening agent is phenyl glycidyl ether.
The silane coupling agent is KH 560.
The underfill adhesive for packaging the 5G equipment chip provided by the invention has the following beneficial effects: 1) naphthyl groups introduced into the blending modified epoxy resin and phenyl groups introduced into the curing agent have a very high molar volume V value, and cyclohexyl in the curing agent also has a low molar polarizability P value, so that the dielectric constant of the filling adhesive can be remarkably reduced; 2) the mixed heat-conducting filler adopting the spherical graphite and the hollow glass beads can greatly improve the heat-conducting property of the filling adhesive. The method can well meet the severe requirements of the prior high-power and high-frequency 5G communication on equipment packaging materials.
Detailed Description
The present invention will be described in further detail with reference to the following examples, but the embodiments of the present invention are not limited thereto.
The following methods were used in the following examples: step 1, weighing 30ml of 1-naphthol, 3ml of benzyltriethylammonium chloride and 67ml of epichlorohydrin in a three-neck flask with the volume ratio of 30:3:67, installing a condenser tube, magnetically stirring, reacting at 50 ℃ for 2 hours, and cooling to room temperature. 5ml of sodium hydroxide solution (C7.5 mol/L) was added dropwise via a constant pressure dropping funnel at a dropping rate of 1 d/s. Reacting at 50 ℃ for 2-4h at constant temperature, cooling to room temperature, washing with deionized water to be neutral, separating out an organic phase, and carrying out reduced pressure rotary evaporation on the hydrated epichlorohydrin in the organic phase to obtain the epoxy resin modified by epoxy hydroxyl of epoxy propane substituted naphthol. And 2, blending and modifying the low-molecular-weight naphthol modified epoxy resin obtained in the step 2 and epoxy resin, sequentially adding a curing agent, a heat-conducting filler, a toughening agent and a silane coupling agent, fully and uniformly mixing in a beaker, and performing vacuum defoaming treatment to obtain the underfill.
Example 1
Blending and modifying 10 parts of the low molecular weight naphthol modified epoxy resin prepared in the step 1 and 90 parts of bisphenol A epoxy resin, and sequentially adding 5 parts of cyclohexylamine serving as a curing agent, 10 parts of spherical graphite and hollow glass microspheres with a heat-conducting filler in a mass ratio of 1:1, 1 part of phenyl glycidyl ether serving as a toughening agent and KH 5600.1 parts of a silane coupling agent according to the proportion of 70 parts of the blended and modified epoxy resin. And (3) fully and uniformly mixing in a beaker, and performing vacuum defoaming treatment to obtain the underfill.
Example 2
Blending and modifying 10 parts of the low-molecular-weight naphthol modified epoxy resin prepared in the step 1 and 90 parts of bisphenol F epoxy resin, and sequentially adding 5 parts of a mixture of cyclohexylamine and benzotriazole with the mass ratio of 1:1 as a curing agent, 15 parts of spherical graphite and hollow glass beads with the mass ratio of 1:1 as a heat-conducting filler, 3 parts of a toughening agent phenyl glycidyl ether and KH 5600.3 parts of a silane coupling agent according to the proportion of 80 parts of the blended and modified epoxy resin. And (3) fully and uniformly mixing in a beaker, and performing vacuum defoaming treatment to obtain the underfill.
Example 3
Blending and modifying 10 parts of the low-molecular-weight naphthol modified epoxy resin prepared in the step 1 and 90 parts of bisphenol F epoxy resin, sequentially adding 10 parts of a mixture of cyclohexylamine and benzotriazole in a mass ratio of 1:1 as a curing agent, 20 parts of spherical graphite and hollow glass beads in a mass ratio of 1:1 as a heat-conducting filler, 5 parts of a toughening agent phenyl glycidyl ether and KH 5600.3 parts of a silane coupling agent according to the proportion of 83.9 parts of the blended and modified epoxy resin. And (3) fully and uniformly mixing in a beaker, and performing vacuum defoaming treatment to obtain the underfill.
The underfill prepared in examples 1-3 were subjected to dielectric constant, dielectric loss tangent and cold-thermal shock cycle testing, respectively, and compared to conventional underfill materials on the market, and the results are shown in the following table:
the test result shows that the performance index of the product in the embodiment is greatly superior to that of the existing product.
Claims (6)
1. A preparation method of underfill for packaging a 5G device chip comprises the following steps:
step 1:
weighing 30ml of 1-naphthol, 3ml of benzyltriethylammonium chloride and 67ml of epichlorohydrin in a 250ml three-neck flask according to the volume ratio of 30:3:67, installing a condensing tube, carrying out magnetic stirring, reacting at 50 ℃ for 2 hours, and cooling to room temperature; dropping 5ml of C =7.5mol/L sodium hydroxide solution in a constant pressure dropping funnel mode at a dropping speed of 1 d/s; reacting at 50 ℃ for 2-4h at constant temperature, cooling to room temperature, washing with deionized water to neutrality, separating out an organic phase, and carrying out reduced pressure rotary distillation on the hydrated epichlorohydrin in the organic phase to obtain 3- (1-naphthoxy) -1, 2-epoxypropane; the reaction formula is as follows:
step 2:
blending and modifying 10 parts of 3- (1-naphthoxy) -1, 2-epoxypropane prepared in the step 1 and 90 parts of epoxy resin, and sequentially adding 5-10 parts of curing agent, 10-20 parts of heat-conducting filler, 1-5 parts of phenyl glycidyl ether and 0.1-0.3 part of silane coupling agent according to the proportion of 70-83.9 parts of the blended and modified epoxy resin; and (3) fully and uniformly mixing in a beaker, and performing vacuum defoaming treatment to obtain the underfill.
2. The method of claim 1, wherein the epoxy resin is one or a mixture of bisphenol A epoxy resin, bisphenol F epoxy resin, or biphenyl epoxy resin.
3. The method for preparing the underfill according to claim 1, wherein the curing agent is one or a mixture of cyclohexylamine and benzotriazole.
4. The method according to claim 1, wherein the heat conductive filler is a mixture of spherical graphite particles having an average particle size of 1-2 μm and hollow glass beads having an average particle size of 3-5 μm; the mass ratio of the mixture is 1: 1.
5. The method of claim 1, wherein the silane coupling agent is KH 560.
6. An underfill adhesive suitable for 5G device chip packaging, prepared by the preparation method of any one of claims 1 to 5.
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| CN113122172B true CN113122172B (en) | 2022-09-16 |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1405199A (en) * | 2002-10-25 | 2003-03-26 | 中国科学院广州化学研究所 | Polyfunctional epoxy resin and its preparation method |
| WO2013035808A1 (en) * | 2011-09-08 | 2013-03-14 | 日本化薬株式会社 | Epoxy resin, epoxy resin composition, and cured product thereof |
| WO2020196604A1 (en) * | 2019-03-27 | 2020-10-01 | 日鉄ケミカル＆マテリアル株式会社 | Naphthol resin, epoxy resin, epoxy resin composition, and cured products thereof |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101522792B (en) * | 2006-10-02 | 2013-01-09 | 日立化成工业株式会社 | Epoxy resin molding material for sealing and electronic component device |
| CN102443138A (en) * | 2011-10-18 | 2012-05-09 | 广东生益科技股份有限公司 | Epoxy resin composition as well as prepreg and copper-foil-clad laminated board prepared by using same |
| CN107828358B (en) * | 2017-10-12 | 2021-05-04 | 烟台德邦科技股份有限公司 | Low-dielectric-constant environment-friendly underfill and preparation method thereof |
| CN108641645A (en) * | 2018-03-29 | 2018-10-12 | 江苏矽时代材料科技有限公司 | A kind of encapsulating semiconductor packaging plastic and preparation method thereof |
| CN109651596B (en) * | 2018-12-24 | 2021-11-09 | 上海华谊树脂有限公司 | Epoxy resin containing naphthalene ring structure and preparation method thereof |
| CN110144186B (en) * | 2019-04-12 | 2021-05-07 | 江苏矽时代材料科技有限公司 | Filler-free underfill adhesive and preparation method thereof |
| CN111440575B (en) * | 2020-03-27 | 2021-07-27 | 顺德职业技术学院 | Special low-dielectric high-thermal-conductivity underfill adhesive for chip packaging |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1405199A (en) * | 2002-10-25 | 2003-03-26 | 中国科学院广州化学研究所 | Polyfunctional epoxy resin and its preparation method |
| WO2013035808A1 (en) * | 2011-09-08 | 2013-03-14 | 日本化薬株式会社 | Epoxy resin, epoxy resin composition, and cured product thereof |
| WO2020196604A1 (en) * | 2019-03-27 | 2020-10-01 | 日鉄ケミカル＆マテリアル株式会社 | Naphthol resin, epoxy resin, epoxy resin composition, and cured products thereof |
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